Vacation rentals in Andersonville

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 118 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Guest favorite

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

4.99 out of 5 average rating, 145 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Guest suite in Andersonville

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

4.96 out of 5 average rating, 378 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

A spacious living room is featured, with a large blue sofa adorned with pink cushions. Two cozy armchairs with blue upholstery flank a glass coffee table, which is positioned on a decorative area rug. A television stands against the wall, while soft lighting illuminates the space.

4.98 out of 5 average rating, 264 reviews

Foster Flat - Retreat to your Home Away from Home

The perfect place to stay for your next trip to Chicago. This fully furnished 2 bedroom/1 bath unit features bright living spaces with modern decor. Located just a few blocks from the heart of Andersonville, you'll find coffee shops, restaurants, shopping and nightlife. Lincoln Square and Ravenswood neighborhoods are also nearby for you to explore. Conveniently located to public transportation (buses, Red and Brown Line trains, as well as Metra), you'll have no trouble getting around town.

A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.

4.97 out of 5 average rating, 104 reviews

Bright 2BR Andersonville – Walk to Lake & Dining

Steps to Chicago’s lakefront, dining, and summer festivals — your bright Andersonville retreat awaits! Wake up to tree-lined streets, stroll to cozy cafes and local boutiques, or spend the afternoon exploring Lake Michigan’s shores. This stylish 2BR flat blends vintage charm with modern comforts—ideal for couples, remote workers, and weekend explorers. Enjoy Superhost hospitality, fast Wi-Fi, and a fully stocked kitchen for a stay that feels like home. We can't wait to welcome you soon!

The bright living area features a grey sofa adorned with colorful cushions. Two teal chairs are positioned nearby, adding a pop of color. Natural light floods the space through oversized windows, highlighting the vibrant artwork on the wall and a modern coffee table at the center.

4.95 out of 5 average rating, 571 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Superhost

A spacious king size bed is dressed in a dark blue patterned quilt, complemented by decorative pillows. A vibrant red throw rests at the foot of the bed. The room features wooden accents, a mirror, and a small bookshelf. Decorative wall hangings add character.

Guest suite in Andersonville

4.86 out of 5 average rating, 377 reviews

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

Guest favorite

A spacious living area is adorned with floral wallpaper, featuring a comfortable gray sofa and a wooden coffee table. Two white chairs are positioned around a woven rug. An open kitchen area is visible, equipped with modern appliances and green bar stools at the counter.

Apartment in Chicago

4.93 out of 5 average rating, 153 reviews

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

4.98 out of 5 average rating, 175 reviews

A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.

Apartment in Chicago

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

A cozy living area features a red sofa adorned with pillows, a brown leather armchair, and a patterned area rug. Walls are decorated with framed artwork, and a dining area is visible in the background with a round table and chairs.

4.97 out of 5 average rating, 207 reviews

Beautiful Hollywood-Ridge Suite in Edgewater

Beautiful, complete, and private apartment/suite in a historic Chicago Greystone located in the beautiful and diverse Edgewater neighborhood. Sleeps 1-4 persons (Queen bed in master bedroom and Deluxe Memory-Foam Queen Size Sofa Sleeper in living area). Suite features guest-controlled central air and heat, 2 flat screen TVs, private bath and shower, and full access to all rooms.

A cozy living area is presented with a dark sofa and a wooden coffee table atop a patterned rug. Exposed brick walls and timber beams enhance the aesthetic. A decorative bicycle hangs on the wall, complemented by shelves displaying art and greenery.

4.96 out of 5 average rating, 106 reviews

Andersonville Bicycle Studio

Enjoy a stylish experience at this centrally-located Andersonville studio. The Bicycle Studio leaves no detail untouched - modern amenities with the charm of exposed brick and timber beams. You are two blocks away from Chicago's popular Andersonville neighborhood - endless dining, shopping and entertainment. Quick access to public transportation and Chicago's lakefront.

A cozy bedroom is depicted with a spacious bed featuring white linens. On either side, elegant lamps provide soft lighting. A colorful artwork adorns the wall above the bed, and framed art pieces are visible on the nearby walls, contributing to the room's inviting feel.